Denatured alcohol containing an acetylated hardwood oil



Patented May 14, i940 DENATURED ALCOHOL CONTAINING AN ACETYLATED HARDWOOD OIL Louis J. F gs, Jn, Kingsport, Tenn, assignor to Eastman Kodak Company, Rochester, N. 2., a corporation of New Jersey No Drawing. Application September 18, 1937, Serial No. 164,572

12 Claims. (Cl. 202- 77) This invention relates to the denaturing of in sodium hydroxide solution and in water. The ethyl alcohol to compositions for use as dena acetylated oil is then vacuum distilled, a very turants, and to alcohol. so denatured. pale, lemon-yellow material with a pleasant It is an object of my invention to provide a odor being produced. 5 denaturant which will render ethyl alcohol con- It will be understood that other methods of 5 taining it unfit for use as a beverage, which canacetylation may be employed. not be economically removed from the alcohol by If only the caustic-soluble hardwood oil is any known methods, which will not render the alused in the acetylation, the resulting products cohol unfit for industrial uses in which denatured are useful as perfume bases, as well as for dealcohol has customarily been employed, and maturing. 10 which will be free from methanol. Other objects In denaturing ethyl alcohol with my novel will hereinafter appear. acetylated hardwood oils, I may use from 1 to 5 I have discovered that the products resulting parts of acetylated wood oil, or even more, per 100 from acetylation of the caustic-soluble oils 010- parts of 95% ethyl alcohol. This imparts a distained in the destructive distillation of hard" agreeable taste, but does not cause the alcohol to 15 woods are effective denaturants for alcohol. have an objectionable odor. The acetylated wood The oils obtained in the destructive distillation oil may be used alone in denaturing, or it may be of hardwood boil from 150 C. to 310 C. They used in conjunction with other denaturing maare of very complex composition, approximately terials derived from the destructive distillation of seventy different compounds, of many different hardwood, such as those which are described in 20 chemical classes. having been identified in them. my U. S. Patents 1,975,090; 1,975,091 and 1,197,-

I prefer to use that fraction of the oils which 092, or with any other denaturants with which it boils between 180 C. and 240 0., although I may may be found to be compatible. use the oil of the entire boiling range, or I may While I have described the acetylation of harde other fr c i n Appr x m y 0% of these wood oil, and the use of acetylated hardwood 2s oils form sodium salts with sodium hydroxide oil as a denaturant, I may propionylate or butyand are known as caustic-soluble oils, while the rylate hardwood oil in the same manner, using the remainder of the oils do not react with sodium corresponding acid anhydride. The acylated hydroxide and are known as neutral oils. For hardwood oils thus produced may likewise be used aceytlation, I may use either the caustic-soluble fo denaturing thyl alcohol, in the ame pr p r- 30 oils or a mixture of both. The acetylation of ti s a etymted hard ood oil. the oils may be carried out as follows: What I claim as my invention and desire to be An excess of 95% acetic anhydride 200 gr secured by Letters Patent of the United States and 25 grams of fused sodium acetate are placed i n a r a t o vessel equipped with an agitator 1. An odorant especially adapted to be used as as and a reflux condenser. The mixture is refluxed a denaturant, comprising t e composition tuntil the approximate, boiling point of acetic ing from the acetylation of a caustic-soluble anhydrideis re ched. 400 grams ofhardwocd oil oil obtained by the destructive distillation of are then slowly added to the mixture, with conhardwoo Stant agitation refluxing being maintained F 2. An odorant especially adapted to be used as 40 Vapor temperature gradually decreases mm} It a denaturant, comprising the composition resultbeen reduced to ki when an of t ing from the acetylation of a caustic-soluble por- 011 has added .Thls 15 to h converslpn tion of a fraction of the oil obtained by the 12515: is i l lix e d 333121 122255; olo g fl gg destructive distillation of hardwood whose boilof the hardwood oil has been completed. The mg t 1S betwefn approxlmately 180 and mixture is then poured into water, and allowed approximately 240 to stand until all of the residual acetic anhydride Penatured ethyl alcohol contalnlng a comhas reacted with water. The acetylated oil is Posltlon resultmg from the acetylatmn a separated fr the acetic acid solution and caustic-soluble oil obtained by the destructive 5o washed with water, then with a 1% sodium cardist l a o of hardwood bonate solution, and finally with a second water 4. Denatured ethyl alcohol containing a comwash. A yield of 565 grams of acetylated hardposition resulting from the acetylation of the wood oil is obtained. The product is light yellow caustic-soluble portion of a fraction of the oil in color, has a pleasant odor, and is insoluble obtained by the destructive distillation of hard- 55 wood whose boiling range is between approximately 180 C. and approximately 240 C.

5. Denatured ethyl alcohol containing, per 109 parts" of 95 ethyl alcohol, from 1 to 5 parts, ap-

proximately, of a composition resulting from the radical containing from 2 to 4 carbon atoms into acaustic-soluble oil. obtained by the destructive distillation ofv hardwood.

8; An odorant especially adapted; to be med as a denaturant, comprising the composition resuiting from the introduction of a fatty acyl radical containing from 2 to carbon atoms into the: caustic soluble portion of a fraction of the oi-lobtained by the destructive distillation of hardwood! whose boiling range is between ap proximately 180 C. and approximately 240 C.

.9. Denatured ethyl alcohol containing a composition resulting from the introduction of a fatty acyl radical containing from 2 to 4 carbon atoms into a caustic-soluble oil obtained by the destructive distillation of hardwood.

l0. Denatured ethyl alcohol containing a composition resulting from the introduction of a fatty acyl radical containing 'from- 2 to; carbon atoms into the caustic-soluble portion of a fraction of he oil obtained by the destructive distillation of hardwood whose; boiling range is between approximately 180 C. and approximately 240 C.

11. Denatured ethyl alcohol containing, ,per IQG partsv 95% ethyl alcohol, from 1 to 5 parts, approximately, of a composition resulting from tbe'introductionof 'a fatty acyl radical containing,- from 2 to 4 carbon atoms into the causticsolubleiportion of an oil obtained by the destructive distillation of hardwood.

332. Denatured ethyl alcohol containing, per lilo-parts of 95% ethyl alcohol, from 1. to 5 parts, approximately, of a composition resulting vfrom the introduction of a fatty acyl radical containing'frcm 2 to 4% carbon atoms into the causticsoluble portion of a fraction of the oil obtained by the destructive distillation: of hardwood whose boiling range is between approximately 180 C. and approximately 240 C.

LOUIS. J. FIGG,. JR-z 

